JP2015524826A5 - - Google Patents
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- JP2015524826A5 JP2015524826A5 JP2015526836A JP2015526836A JP2015524826A5 JP 2015524826 A5 JP2015524826 A5 JP 2015524826A5 JP 2015526836 A JP2015526836 A JP 2015526836A JP 2015526836 A JP2015526836 A JP 2015526836A JP 2015524826 A5 JP2015524826 A5 JP 2015524826A5
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- JP
- Japan
- Prior art keywords
- phenyl
- ethyl
- pyrimidin
- amino
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000001875 compounds Chemical class 0.000 claims 54
- 125000000217 alkyl group Chemical group 0.000 claims 49
- 229910052799 carbon Inorganic materials 0.000 claims 36
- 125000001424 substituent group Chemical group 0.000 claims 33
- -1 cyclopropylidene, cyclobutylidene, cyclopentylidene Chemical group 0.000 claims 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 22
- 229940002612 prodrug Drugs 0.000 claims 21
- 239000000651 prodrug Substances 0.000 claims 21
- 150000003839 salts Chemical class 0.000 claims 21
- 239000012453 solvate Substances 0.000 claims 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 16
- 239000000203 mixture Substances 0.000 claims 10
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 9
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims 8
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 238000000034 method Methods 0.000 claims 8
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 6
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- RTGQEFNYCLEWPU-UHFFFAOYSA-N 1-[2-[2-[2-[(6-piperidin-4-ylpyridin-3-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C=1C=CC=C(CCC=2C(=CN=C(NC=3C=NC(=CC=3)C3CCNCC3)N=2)C(F)(F)F)C=1C1(C(=O)N)CC1 RTGQEFNYCLEWPU-UHFFFAOYSA-N 0.000 claims 4
- QXWHXZVEZDYDHA-UHFFFAOYSA-N 1-[2-[2-[2-[4-(azetidin-3-yl)anilino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C=1C=CC=C(CCC=2C(=CN=C(NC=3C=CC(=CC=3)C3CNC3)N=2)C(F)(F)F)C=1C1(C(=O)N)CC1 QXWHXZVEZDYDHA-UHFFFAOYSA-N 0.000 claims 3
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims 3
- 101000851030 Homo sapiens Vascular endothelial growth factor receptor 3 Proteins 0.000 claims 3
- 102100033179 Vascular endothelial growth factor receptor 3 Human genes 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- XJUWQWGUVDBHQJ-UHFFFAOYSA-N 1-[2-[2-[2-(4-piperidin-4-ylanilino)-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]cyclobutane-1-carboxamide Chemical compound C=1C=CC=C(CCC=2C(=CN=C(NC=3C=CC(=CC=3)C3CCNCC3)N=2)C(F)(F)F)C=1C1(C(=O)N)CCC1 XJUWQWGUVDBHQJ-UHFFFAOYSA-N 0.000 claims 2
- YCIIZJUIBNPNED-UHFFFAOYSA-N 1-[2-[2-[2-(4-piperidin-4-ylanilino)-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C=1C=CC=C(CCC=2C(=CN=C(NC=3C=CC(=CC=3)C3CCNCC3)N=2)C(F)(F)F)C=1C1(C(=O)N)CC1 YCIIZJUIBNPNED-UHFFFAOYSA-N 0.000 claims 2
- MHBVMQSXQLYCRO-UHFFFAOYSA-N 1-[2-[2-[2-[(6-acetylpyridin-3-yl)amino]-5-chloropyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C1=NC(C(=O)C)=CC=C1NC1=NC=C(Cl)C(CCC=2C(=CC=CC=2)C2(CC2)C(N)=O)=N1 MHBVMQSXQLYCRO-UHFFFAOYSA-N 0.000 claims 2
- REZLRWDJAZYYMQ-UHFFFAOYSA-N 1-[2-[2-[2-[(6-methoxypyridin-3-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(C(F)(F)F)C(CCC=2C(=CC=CC=2)C2(CC2)C(N)=O)=N1 REZLRWDJAZYYMQ-UHFFFAOYSA-N 0.000 claims 2
- TVHISEZISKGSQX-UHFFFAOYSA-N 1-[2-[2-[2-[4-(1-aminoethyl)anilino]-5-methylpyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C1=CC(C(N)C)=CC=C1NC1=NC=C(C)C(CCC=2C(=CC=CC=2)C2(CC2)C(N)=O)=N1 TVHISEZISKGSQX-UHFFFAOYSA-N 0.000 claims 2
- RLIHQICAODIXMW-UHFFFAOYSA-N 1-[2-[2-[2-[4-(1-methylpiperidin-4-yl)anilino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C1CN(C)CCC1C(C=C1)=CC=C1NC1=NC=C(C(F)(F)F)C(CCC=2C(=CC=CC=2)C2(CC2)C(N)=O)=N1 RLIHQICAODIXMW-UHFFFAOYSA-N 0.000 claims 2
- FBOOAKYRDMGTPS-UHFFFAOYSA-N 1-[2-[2-[2-[[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]amino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C1CN(C)CCC1N1N=CC(NC=2N=C(CCC=3C(=CC=CC=3)C3(CC3)C(N)=O)C(=CN=2)C(F)(F)F)=C1 FBOOAKYRDMGTPS-UHFFFAOYSA-N 0.000 claims 2
- HQRUNGNEQLUCLO-UHFFFAOYSA-N 1-[2-[2-[2-[[1-(azetidin-3-yl)pyrazol-4-yl]amino]-5-chloropyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C=1C=CC=C(CCC=2C(=CN=C(NC3=CN(N=C3)C3CNC3)N=2)Cl)C=1C1(C(=O)N)CC1 HQRUNGNEQLUCLO-UHFFFAOYSA-N 0.000 claims 2
- ADECUQYWGSIQCQ-UHFFFAOYSA-N 1-[2-[2-[2-[[6-(1-aminoethyl)pyridin-3-yl]amino]-5-chloropyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C1=NC(C(N)C)=CC=C1NC1=NC=C(Cl)C(CCC=2C(=CC=CC=2)C2(CC2)C(N)=O)=N1 ADECUQYWGSIQCQ-UHFFFAOYSA-N 0.000 claims 2
- DQQWJKOTZMUAHI-UHFFFAOYSA-N 1-[2-[2-[2-[[6-(1-methylpiperidin-4-yl)pyridin-3-yl]amino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C1CN(C)CCC1C(N=C1)=CC=C1NC1=NC=C(C(F)(F)F)C(CCC=2C(=CC=CC=2)C2(CC2)C(N)=O)=N1 DQQWJKOTZMUAHI-UHFFFAOYSA-N 0.000 claims 2
- PXZFWIYLLCBPCU-UHFFFAOYSA-N 1-[2-[2-[5-chloro-2-[(1,3-dimethylpyrazol-4-yl)amino]pyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound CC1=NN(C)C=C1NC1=NC=C(Cl)C(CCC=2C(=CC=CC=2)C2(CC2)C(N)=O)=N1 PXZFWIYLLCBPCU-UHFFFAOYSA-N 0.000 claims 2
- KUZRTSMZHWGUIV-UHFFFAOYSA-N 1-[2-[2-[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(CCC=2C(=CC=CC=2)C2(CC2)C(N)=O)=N1 KUZRTSMZHWGUIV-UHFFFAOYSA-N 0.000 claims 2
- GVZZEKBXTZEWOA-UHFFFAOYSA-N 1-[2-[2-[5-chloro-2-[(1-piperidin-4-ylpyrazol-4-yl)amino]pyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C=1C=CC=C(CCC=2C(=CN=C(NC3=CN(N=C3)C3CCNCC3)N=2)Cl)C=1C1(C(=O)N)CC1 GVZZEKBXTZEWOA-UHFFFAOYSA-N 0.000 claims 2
- MPAJFLQBHBSWNO-UHFFFAOYSA-N 1-[2-[2-[5-chloro-2-[(1-propan-2-ylpyrazol-4-yl)amino]pyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C1=NN(C(C)C)C=C1NC1=NC=C(Cl)C(CCC=2C(=CC=CC=2)C2(CC2)C(N)=O)=N1 MPAJFLQBHBSWNO-UHFFFAOYSA-N 0.000 claims 2
- UMAZVUGSOHOIKQ-UHFFFAOYSA-N 1-[2-[2-[5-chloro-2-[(1-pyrrolidin-3-ylpyrazol-4-yl)amino]pyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C=1C=CC=C(CCC=2C(=CN=C(NC3=CN(N=C3)C3CNCC3)N=2)Cl)C=1C1(C(=O)N)CC1 UMAZVUGSOHOIKQ-UHFFFAOYSA-N 0.000 claims 2
- YNPZQOCKZKZHEM-UHFFFAOYSA-N 1-[2-[2-[5-chloro-2-[(6-piperidin-4-ylpyridin-3-yl)amino]pyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C=1C=CC=C(CCC=2C(=CN=C(NC=3C=NC(=CC=3)C3CCNCC3)N=2)Cl)C=1C1(C(=O)N)CC1 YNPZQOCKZKZHEM-UHFFFAOYSA-N 0.000 claims 2
- VDXARSHJPFZWJT-UHFFFAOYSA-N 1-[2-[2-[5-chloro-2-[4-(1-methylpiperidin-4-yl)anilino]pyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C1CN(C)CCC1C(C=C1)=CC=C1NC1=NC=C(Cl)C(CCC=2C(=CC=CC=2)C2(CC2)C(N)=O)=N1 VDXARSHJPFZWJT-UHFFFAOYSA-N 0.000 claims 2
- GZQZGOLXVRSKEE-UHFFFAOYSA-N 1-[2-[2-[5-chloro-2-[[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]amino]pyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C1CN(C)CCC1N1N=CC(NC=2N=C(CCC=3C(=CC=CC=3)C3(CC3)C(N)=O)C(Cl)=CN=2)=C1 GZQZGOLXVRSKEE-UHFFFAOYSA-N 0.000 claims 2
- SXYKWFQBPFJOFP-UHFFFAOYSA-N 1-[2-[2-[5-chloro-2-[[1-(2,2,2-trifluoroethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C=1C=CC=C(CCC=2C(=CN=C(NC3=CN(CC(F)(F)F)N=C3)N=2)Cl)C=1C1(C(=O)N)CC1 SXYKWFQBPFJOFP-UHFFFAOYSA-N 0.000 claims 2
- PTKYIKLVYSCLGO-UHFFFAOYSA-N 1-[2-[2-[5-chloro-2-[[1-(difluoromethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C=1C=CC=C(CCC=2C(=CN=C(NC3=CN(N=C3)C(F)F)N=2)Cl)C=1C1(C(=O)N)CC1 PTKYIKLVYSCLGO-UHFFFAOYSA-N 0.000 claims 2
- MZYDUEWRHJEHIO-UHFFFAOYSA-N 1-[2-[2-[5-chloro-2-[[6-(trifluoromethyl)pyridin-3-yl]amino]pyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C=1C=CC=C(CCC=2C(=CN=C(NC=3C=NC(=CC=3)C(F)(F)F)N=2)Cl)C=1C1(C(=O)N)CC1 MZYDUEWRHJEHIO-UHFFFAOYSA-N 0.000 claims 2
- IGVRMTANTIJHGI-UHFFFAOYSA-N 1-[2-[2-[5-methyl-2-(1h-pyrazol-4-ylamino)pyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound N1=C(CCC=2C(=CC=CC=2)C2(CC2)C(N)=O)C(C)=CN=C1NC=1C=NNC=1 IGVRMTANTIJHGI-UHFFFAOYSA-N 0.000 claims 2
- HSBIEJWYEOZFNZ-UHFFFAOYSA-N 1-[2-[2-[5-methyl-2-[[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]amino]pyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C1CN(C)CCC1N1N=CC(NC=2N=C(CCC=3C(=CC=CC=3)C3(CC3)C(N)=O)C(C)=CN=2)=C1 HSBIEJWYEOZFNZ-UHFFFAOYSA-N 0.000 claims 2
- ADIYOWKIIDYVOH-UHFFFAOYSA-N 1-[2-[2-[5-methyl-2-[[6-(1-methylpiperidin-4-yl)pyridin-3-yl]amino]pyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C1CN(C)CCC1C(N=C1)=CC=C1NC1=NC=C(C)C(CCC=2C(=CC=CC=2)C2(CC2)C(N)=O)=N1 ADIYOWKIIDYVOH-UHFFFAOYSA-N 0.000 claims 2
- ARYYRYQHTRJHNJ-UHFFFAOYSA-N 1-[3-[2-[2-[(1-piperidin-4-ylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C=1C=CC(CCC=2C(=CN=C(NC3=CN(N=C3)C3CCNCC3)N=2)C(F)(F)F)=CC=1C1(C(=O)N)CC1 ARYYRYQHTRJHNJ-UHFFFAOYSA-N 0.000 claims 2
- PHYAXSDYUXZTPA-UHFFFAOYSA-N 2-[2-[2-[2-(1h-pyrazol-4-ylamino)-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]propanamide Chemical compound NC(=O)C(C)C1=CC=CC=C1CCC1=NC(NC2=CNN=C2)=NC=C1C(F)(F)F PHYAXSDYUXZTPA-UHFFFAOYSA-N 0.000 claims 2
- MVRXYLMTEFAMSR-UHFFFAOYSA-N 2-[2-[2-[2-(4-piperidin-4-ylanilino)-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]butanamide Chemical compound CCC(C(N)=O)C1=CC=CC=C1CCC1=NC(NC=2C=CC(=CC=2)C2CCNCC2)=NC=C1C(F)(F)F MVRXYLMTEFAMSR-UHFFFAOYSA-N 0.000 claims 2
- MXIBXHRQUQYGTB-UHFFFAOYSA-N 2-[2-[2-[2-[(6-methoxypyridin-3-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]propanamide Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(C(F)(F)F)C(CCC=2C(=CC=CC=2)C(C)C(N)=O)=N1 MXIBXHRQUQYGTB-UHFFFAOYSA-N 0.000 claims 2
- YTRSVLZQCGGZCG-UHFFFAOYSA-N 2-[2-[2-[2-[(6-piperidin-4-ylpyridin-3-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]propanamide Chemical compound NC(=O)C(C)C1=CC=CC=C1CCC1=NC(NC=2C=NC(=CC=2)C2CCNCC2)=NC=C1C(F)(F)F YTRSVLZQCGGZCG-UHFFFAOYSA-N 0.000 claims 2
- LOCJSNMNHUBLPB-UHFFFAOYSA-N 2-[2-[2-[2-[[1-(1-acetylpiperidin-4-yl)pyrazol-4-yl]amino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]propanamide Chemical compound NC(=O)C(C)C1=CC=CC=C1CCC1=NC(NC2=CN(N=C2)C2CCN(CC2)C(C)=O)=NC=C1C(F)(F)F LOCJSNMNHUBLPB-UHFFFAOYSA-N 0.000 claims 2
- UWFYHPLYALSION-UHFFFAOYSA-N 2-[2-[2-[2-[[1-(1-ethylpiperidin-4-yl)pyrazol-4-yl]amino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]propanamide Chemical compound C1CN(CC)CCC1N1N=CC(NC=2N=C(CCC=3C(=CC=CC=3)C(C)C(N)=O)C(=CN=2)C(F)(F)F)=C1 UWFYHPLYALSION-UHFFFAOYSA-N 0.000 claims 2
- RJUAJPXDDBGVQP-UHFFFAOYSA-N 2-[2-[2-[2-[[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]amino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]propanamide Chemical compound NC(=O)C(C)C1=CC=CC=C1CCC1=NC(NC2=CN(N=C2)C2CCN(C)CC2)=NC=C1C(F)(F)F RJUAJPXDDBGVQP-UHFFFAOYSA-N 0.000 claims 2
- DNXYDLQSAQHEQD-UHFFFAOYSA-N 2-[2-[2-[2-[[1-(1-propan-2-ylpiperidin-4-yl)pyrazol-4-yl]amino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]propanamide Chemical compound C1CN(C(C)C)CCC1N1N=CC(NC=2N=C(CCC=3C(=CC=CC=3)C(C)C(N)=O)C(=CN=2)C(F)(F)F)=C1 DNXYDLQSAQHEQD-UHFFFAOYSA-N 0.000 claims 2
- JGVFAQMWQRTRLJ-UHFFFAOYSA-N 2-[2-[2-[5-chloro-2-(pyridazin-4-ylamino)pyrimidin-4-yl]ethyl]phenyl]propanamide Chemical compound NC(=O)C(C)C1=CC=CC=C1CCC1=NC(NC=2C=NN=CC=2)=NC=C1Cl JGVFAQMWQRTRLJ-UHFFFAOYSA-N 0.000 claims 2
- VYDHVXKWBJAYCG-UHFFFAOYSA-N 2-[2-[2-[5-chloro-2-(pyridin-3-ylamino)pyrimidin-4-yl]ethyl]phenyl]propanamide Chemical compound NC(=O)C(C)C1=CC=CC=C1CCC1=NC(NC=2C=NC=CC=2)=NC=C1Cl VYDHVXKWBJAYCG-UHFFFAOYSA-N 0.000 claims 2
- INJXBWVPVJXXSO-UHFFFAOYSA-N 2-[2-[2-[5-chloro-2-(pyrimidin-5-ylamino)pyrimidin-4-yl]ethyl]phenyl]propanamide Chemical compound NC(=O)C(C)C1=CC=CC=C1CCC1=NC(NC=2C=NC=NC=2)=NC=C1Cl INJXBWVPVJXXSO-UHFFFAOYSA-N 0.000 claims 2
- GGJRNPWQYMGFOS-UHFFFAOYSA-N 2-[2-[2-[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]ethyl]phenyl]-2-methylpropanamide Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(CCC=2C(=CC=CC=2)C(C)(C)C(N)=O)=N1 GGJRNPWQYMGFOS-UHFFFAOYSA-N 0.000 claims 2
- JAHMDTQVHMQVJF-UHFFFAOYSA-N 2-[2-[2-[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]ethyl]phenyl]propanamide Chemical compound NC(=O)C(C)C1=CC=CC=C1CCC1=NC(NC2=CN(C)N=C2)=NC=C1Cl JAHMDTQVHMQVJF-UHFFFAOYSA-N 0.000 claims 2
- FYMHFFRHIPSDGQ-UHFFFAOYSA-N 2-[2-[2-[5-chloro-2-[(1-piperidin-4-ylpyrazol-4-yl)amino]pyrimidin-4-yl]ethyl]phenyl]propanamide Chemical compound NC(=O)C(C)C1=CC=CC=C1CCC1=NC(NC2=CN(N=C2)C2CCNCC2)=NC=C1Cl FYMHFFRHIPSDGQ-UHFFFAOYSA-N 0.000 claims 2
- OCHGDSBDDOYVSU-UHFFFAOYSA-N 2-[2-[2-[5-chloro-2-[(6-methylpyridin-3-yl)amino]pyrimidin-4-yl]ethyl]phenyl]propanamide Chemical compound NC(=O)C(C)C1=CC=CC=C1CCC1=NC(NC=2C=NC(C)=CC=2)=NC=C1Cl OCHGDSBDDOYVSU-UHFFFAOYSA-N 0.000 claims 2
- JKWCRJGFBDYBDW-UHFFFAOYSA-N 2-[2-[2-[5-chloro-2-[(6-piperidin-4-ylpyridin-3-yl)amino]pyrimidin-4-yl]ethyl]phenyl]propanamide Chemical compound NC(=O)C(C)C1=CC=CC=C1CCC1=NC(NC=2C=NC(=CC=2)C2CCNCC2)=NC=C1Cl JKWCRJGFBDYBDW-UHFFFAOYSA-N 0.000 claims 2
- JRSJILWBSZUJGY-UHFFFAOYSA-N 2-[2-[2-[5-methyl-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]ethyl]phenyl]propanamide Chemical compound NC(=O)C(C)C1=CC=CC=C1CCC1=NC(NC2=CN(C)N=C2)=NC=C1C JRSJILWBSZUJGY-UHFFFAOYSA-N 0.000 claims 2
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 230000001668 ameliorated effect Effects 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- GGRQRZPNPBKAKX-UHFFFAOYSA-N tert-butyl n-[1-[4-[[4-[2-[2-(1-carbamoylcyclopropyl)phenyl]ethyl]-5-(trifluoromethyl)pyrimidin-2-yl]amino]phenyl]ethyl]carbamate Chemical compound C1=CC(C(NC(=O)OC(C)(C)C)C)=CC=C1NC1=NC=C(C(F)(F)F)C(CCC=2C(=CC=CC=2)C2(CC2)C(N)=O)=N1 GGRQRZPNPBKAKX-UHFFFAOYSA-N 0.000 claims 2
- YOOZCWNOLYRGFW-UHFFFAOYSA-N tert-butyl n-[1-[4-[[4-[2-[2-(1-carbamoylcyclopropyl)phenyl]ethyl]-5-chloropyrimidin-2-yl]amino]phenyl]ethyl]carbamate Chemical compound C1=CC(C(NC(=O)OC(C)(C)C)C)=CC=C1NC1=NC=C(Cl)C(CCC=2C(=CC=CC=2)C2(CC2)C(N)=O)=N1 YOOZCWNOLYRGFW-UHFFFAOYSA-N 0.000 claims 2
- 238000011282 treatment Methods 0.000 claims 2
- UMEFYEWFNFNLHP-UHFFFAOYSA-N 1-[2-[2-[2-[(1-methylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C1=NN(C)C=C1NC1=NC=C(C(F)(F)F)C(CCC=2C(=CC=CC=2)C2(CC2)C(N)=O)=N1 UMEFYEWFNFNLHP-UHFFFAOYSA-N 0.000 claims 1
- JRVVFSGIVLNBFG-UHFFFAOYSA-N 1-[2-[2-[5-(trifluoromethyl)-2-[[6-(trifluoromethyl)pyridin-3-yl]amino]pyrimidin-4-yl]ethyl]phenyl]cyclopropane-1-carboxamide Chemical compound C=1C=CC=C(CCC=2C(=CN=C(NC=3C=NC(=CC=3)C(F)(F)F)N=2)C(F)(F)F)C=1C1(C(=O)N)CC1 JRVVFSGIVLNBFG-UHFFFAOYSA-N 0.000 claims 1
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| CA2882270A1 (en) | 2012-08-17 | 2014-02-20 | Cancer Therapeutics Crc Pty Limited | Vegfr3 inhibitors |
| WO2015123722A1 (en) * | 2014-02-19 | 2015-08-27 | Bionomics Limited | Inhibitors |
| CN106588884B (zh) * | 2016-11-10 | 2019-04-09 | 浙江大学 | 2-多取代芳环-嘧啶类衍生物及制备和医药用途 |
| CN106588885B (zh) * | 2016-11-10 | 2019-03-19 | 浙江大学 | 2-取代芳环-嘧啶类衍生物及制备和应用 |
| CA3086182A1 (en) * | 2017-12-20 | 2019-06-27 | Denali Therapeutics Inc. | Process for the preparation of pyrimidinyl-4-aminopyrazole compounds |
| US11548908B2 (en) | 2017-12-29 | 2023-01-10 | Glycomimetics, Inc. | Heterobifunctional inhibitors of E-selectin and galectin-3 |
| US11845771B2 (en) | 2018-12-27 | 2023-12-19 | Glycomimetics, Inc. | Heterobifunctional inhibitors of E-selectin and galectin-3 |
| CN109942616A (zh) * | 2019-04-18 | 2019-06-28 | 广东工业大学 | 一种含炔基的芳基酰胺类衍生物及其制备方法和应用 |
| WO2023073148A1 (en) * | 2021-10-29 | 2023-05-04 | Janssen Pharmaceutica Nv | Vascular endothelial growth factor receptor 3 as biomarker for bace2 activity |
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| GB9624482D0 (en) | 1995-12-18 | 1997-01-15 | Zeneca Phaema S A | Chemical compounds |
| CA2242425C (en) | 1996-02-13 | 2006-07-18 | Zeneca Limited | Quinazoline derivatives as vegf inhibitors |
| NZ331191A (en) | 1996-03-05 | 2000-03-27 | Zeneca Ltd | 4-anilinoquinazoline derivatives and pharmaceutical compositions thereof |
| GB9718972D0 (en) | 1996-09-25 | 1997-11-12 | Zeneca Ltd | Chemical compounds |
| ES2284200T3 (es) | 1997-02-12 | 2007-11-01 | Electrophoretics Limited | Marcadores proteicos para cancer de pulmon y uso de los mismos. |
| GB9714249D0 (en) | 1997-07-08 | 1997-09-10 | Angiogene Pharm Ltd | Vascular damaging agents |
| GB9900334D0 (en) | 1999-01-07 | 1999-02-24 | Angiogene Pharm Ltd | Tricylic vascular damaging agents |
| GB9900752D0 (en) | 1999-01-15 | 1999-03-03 | Angiogene Pharm Ltd | Benzimidazole vascular damaging agents |
| EE05345B1 (et) | 1999-02-10 | 2010-10-15 | Astrazeneca Ab | Kinasoliini derivaadid angiogeneesi inhibiitoritena |
| PT1244647E (pt) | 1999-11-05 | 2006-10-31 | Astrazeneca Ab | Derivados de quinazolina como inibidores de vegf |
| HRP20020751B1 (hr) | 2000-02-15 | 2011-01-31 | Sugen | Pirolom supstituirani 2-indolinoni kao inhibitori protein kinaze |
| BR0111230A (pt) | 2000-05-31 | 2003-06-10 | Astrazeneca Ab | Composto, e, uso e processo para a preparação do mesmo |
| UA73993C2 (uk) | 2000-06-06 | 2005-10-17 | Астразенека Аб | Хіназолінові похідні для лікування пухлин та фармацевтична композиція |
| KR20030014425A (ko) | 2000-07-07 | 2003-02-17 | 앤지오젠 파마슈티칼스 리미티드 | 혈관 손상제인 콜치놀 유도체 |
| EE200300015A (et) | 2000-07-07 | 2004-10-15 | Angiogene Pharmaceuticals Limited | Kolhinooli derivaadid kui angiogeneesi inhibiitorid |
| JP4460292B2 (ja) | 2001-10-17 | 2010-05-12 | ベーリンガー インゲルハイム ファルマ ゲゼルシャフト ミット ベシュレンクテル ハフツング ウント コンパニー コマンディトゲゼルシャフト | ピリミジン誘導体、これらの化合物を含む医薬組成物、その使用及びその調製方法 |
| WO2008008234A1 (en) * | 2006-07-07 | 2008-01-17 | Targegen, Inc. | 2-amino-5-substituted pyrimidine inhibitors |
| WO2008076415A1 (en) * | 2006-12-14 | 2008-06-26 | Exelixis, Inc. | Methods of using mek inhibitors |
| TW200922590A (en) * | 2007-09-10 | 2009-06-01 | Curis Inc | VEGFR inhibitors containing a zinc binding moiety |
| MX2011004680A (es) | 2008-11-06 | 2011-05-25 | Astrazeneca Ab | Moduladores de beta amiloide. |
| KR101639642B1 (ko) * | 2008-12-05 | 2016-07-14 | 애브비 바하마스 리미티드 | 암 치료에 사용하기 위한 키나제 억제제로서의 티에노［3,2-ｃ］피리딘 유도체 |
| WO2010111406A2 (en) | 2009-03-24 | 2010-09-30 | Myriad Pharmaceuticals, Inc. | Compounds and therapeutic uses thereof |
| EP2429520A1 (en) * | 2009-05-14 | 2012-03-21 | Boehringer Ingelheim International GmbH | New combination therapy in treatment of oncological and fibrotic diseases |
| DE102010034699A1 (de) | 2010-08-18 | 2012-02-23 | Merck Patent Gmbh | Pyrimidinderivate |
| WO2012036919A2 (en) * | 2010-09-14 | 2012-03-22 | Glaxosmithkline Llc | Combination of braf and vegf inhibitors |
| WO2012110773A1 (en) | 2011-02-17 | 2012-08-23 | Cancer Therapeutics Crc Pty Limited | Fak inhibitors |
| DK2675794T3 (da) * | 2011-02-17 | 2019-05-06 | Cancer Therapeutics Crc Pty Ltd | Selektive fak-inhibitorer |
| KR101682417B1 (ko) | 2011-02-25 | 2016-12-06 | 주식회사유한양행 | 다이아미노피리미딘 유도체 및 그의 제조방법 |
| JP6226981B2 (ja) | 2012-07-17 | 2017-11-08 | サノフイ | 肝細胞癌を処置するためのｖｅｇｆｒ−３阻害剤の使用 |
| WO2014027199A1 (en) * | 2012-08-14 | 2014-02-20 | Cancer Therapeutics Crc Pty Ltd | Fak and flt3 inhibitors |
| CN103113355B (zh) | 2013-02-27 | 2014-08-13 | 无锡爱内特生物科技有限公司 | 一种Bcr/Abl酪氨酸激酶抑制剂及其制备方法和在治疗慢性粒细胞白血病中的应用 |
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- 2013-08-16 AU AU2013302320A patent/AU2013302320A1/en not_active Abandoned
- 2013-08-16 WO PCT/AU2013/000913 patent/WO2014026243A1/en not_active Ceased
- 2013-08-16 CN CN201380052158.7A patent/CN104736533B/zh not_active Expired - Fee Related
- 2013-08-16 EP EP13829265.1A patent/EP2885291A4/en not_active Withdrawn
- 2013-08-16 CA CA2882158A patent/CA2882158A1/en not_active Abandoned
- 2013-08-16 US US14/422,093 patent/US20160009686A1/en not_active Abandoned
- 2013-08-16 US US13/969,037 patent/US9238644B2/en not_active Expired - Fee Related
- 2013-08-16 JP JP2015526836A patent/JP2015524826A/ja active Pending
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